The present invention relates to novel dyes, in particular reactive dyes, a process for their preparation and their use for dyeing or printing textile fibre materials.
The practice of dyeing using reactive dyes has recently led to increased requirements regarding the quality of the dyeings and the profitability of the dyeing process. There consequently continues to be a need for novel reactive dyes which have improved properties in particular in respect of application.
Reactive dyes which have an adequate substantivity and at the same time a good ease of washing off for the unfixed portions are required nowadays for dyeing. They should furthermore have a good tinctorial yield and a high reactivity, and in particular dyeings with high degrees of fixing should be produced. These requirements are not met in all properties by the known dyes.
The present invention is therefore based on the object of discovering novel improved dyes, in particular reactive dyes, which are used for dyeing and printing fibre materials and have the qualities characterized above to a high degree. The novel dyes should have the distinctive features in particular of high fixing yields and high fibre-dye bond stabilities, and furthermore the portions not fixed to the fibre should be easy to wash out. They should furthermore produce dyeings with good all-round properties, for example light- and wetfastness properties.
It has been found that the object described is substantially achieved with the novel dyes defined below.
The present invention therefore relates to dyes of the formula (1) 
in which
Me is Cu or Ni,
R1 is hydrogen or substituted or unsubstituted C1-C4alkyl or R1 is as defined for A,
X1 is halogen, hydroxyl, C1-C4alkoxy, substituted or unsubstituted C1-C4alkylthio or amino or
is an N-heterocyclic radical which may contain further heteroatoms,
u is the number 1, 2, 3 or 4,
q is the number 0 or 1,
the benzene rings I, II or III are unsubstituted or further substituted and
A is a radical of the formula (2a), (2b) or (3) 
in which
B1 and B2 independently of one another are an aliphatic bridge member,
D1 and D2 independently of one another are the radical of a diazo component of the benzene or naphthalene series,
R2 is hydrogen or substituted or unsubstituted C1-C4alkyl,
R3 and R6 independently of one another are hydrogen, cyano, carbamoyl or sulfomethyl,
R4 is hydrogen, C1-C4alkyl or amino,
R5 is amino or N-mono- or N,Nxe2x80x94dixe2x80x94C1-C4alkylamino which are unsubstituted or substituted in the alkyl moiety and
R7 is hydrogen or C1-C4alkyl.
The dyes of the formula (1) contain at least two, preferably 2 to 6, and in particular 2 to 4 sulfo groups, each of which is either in the form of its free acid or, preferably, salts thereof. Salts are, for example, the alkali metal, alkaline earth metal or sodium salts, salts of an organic amine or mixtures thereof. Examples are sodium, lithium, potassium or ammonium salts, the salt of mono-, di- or triethanolamine or Na/Li- or Na/Li/NH4 mixed salts.
Me is preferably Cu.
Substituted or unsubstituted C1-C4alkyl R1 and R2 can be methyl, ethyl, n- or i-propyl or n-, sec-, tert- or isobutyl which are unsubstituted or substituted, for example by hydroxyl, sulfo, sulfato, carboxyl, cyano, halogen, C1-C4alkoxycarbonyl or carbamoyl, in particular by hydroxyl, sulfo, sulfato or carboxyl.
R1 is preferably hydrogen, C1-C4alkyl which is unsubstituted or substituted by hydroxyl, or a radical A, particularly preferably hydrogen, methyl, ethyl or xcex2-hydroxyethyl or a radical A, and especially preferably hydrogen or a radical A.
Halogen X1 is, for example, fluorine, chlorine or bromine.
C1-C4alkoxy X1, is, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy, preferably methoxy or ethoxy, and in particular methoxy.
C1-C4alkylthio X1 is, for example, methylthio, ethylthio, n-propylthio, isopropylthio or n-butylthio, in particular ethylthio or n-propylthio. The radicals mentioned are unsubstituted or substituted in the alkyl moiety by hydroxyl, carboxyl or sulfo. The substituted radicals are preferred.
Substituted or unsubstituted amino X1 is amino which is unsubstituted or substituted on the N atom, for example the following radicals:
N-mono- or N,N- di- C1-C4alkylamino, which includes both the unsubstituted radicals and the radicals substituted in the alkyl moiety, for example by C1-C4-alkoxy, hydroxyl, carboxyl, sulfo or sulfato; the radicals substituted in the alkyl moiety are preferred;
C5-C7-cycloalkylamino, which includes both the unsubstituted radicals, and the radicals substituted in the cycloalkyl ring, for example by C1-C4alkyl, in particular methyl; the corresponding cyclohexyl radicals are preferred such radicals;
phenylamino or Nxe2x80x94C1-C4-alkyl-N-phenylamino, which includes both the unsubstituted radicals and the radicals substituted in the phenyl ring, for example by C1-C4alkyl, C1-C4alkoxy, halogen, carboxyl or sulfo; these radicals are preferably unsubstituted in the phenyl ring or substituted by sulfo.
N-heterocyclic radicals X1 which may contain further heteroatoms are, for example, morpholino or piperidin-1-yl.
X1 is preferably fluorine or chlorine.
u is preferably the number 1, 2 or 3, in particular 2 or 3.
q is preferably the number 1.
Aliphatic bridge members B1 and B2 are, independently of one another, for example, straight-chain or branched C2-C12alkylene which is unsubstituted or substituted by hydroxyl, C1-C4alkoxy, sulfato or sulfo and/or interrupted once or several times by xe2x80x94Oxe2x80x94 or xe2x80x94NRxe2x80x2xe2x80x94, in which Rxe2x80x2 is hydrogen or C1-C4alkyl, preferably hydrogen, methyl or ethyl, and particularly preferably hydrogen. B1 and B2 independently of one another are preferably straight-chain or branched C2-C6alkylene, which is unsubstituted or substituted by hydroxyl, sulfo or sulfato, and particularly preferably unsubstituted straight-chain or branched C2-C6-alkylene. Examples of particularly preferred radicals B1 and B2 are 1,2-ethylene, 1,3-propylene, 2-hydroxy-1,3-propylene, 1,4-butylene, 2-methyl-1,5-pentylene and 1,6-hexylene, in particular 1,2-propylene and 1,2-ethylene, and especially 1,2-ethylene.
Substituents which are customary in dyes are suitable for D1 and D2. Examples are the following: C1-C4alkyl, which is to be understood as meaning methyl, ethyl, n- or isopropyl or n-, iso-, sec- or tert-butyl; C1-C4alkoxy, which is to be understood as meaning methoxy, ethoxy, n- or isopropoxy or n-, iso-, sec- or tert-butoxy; hydroxy-C1-C4alkoxy; phenoxy; C2-C6alkanoylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl or C1-C4alkoxy, for example acetylamino, hydroxyacetylamino, methoxyacetylamino or propionylamino; benzoylamino which is unsubstituted or substituted in the phenyl moiety by hydroxyl, sulfo, halogen, C1-C4alkyl or C1-C4alkoxy; C1-C6alkoxycarbonylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, C1-C4alkyl or C1-C4-alkoxy; phenoxycarbonylamino; which is unsubstituted or substituted in the phenyl moiety by hydroxyl, C1-C4alkyl or C1-C4alkoxy; amino; Nxe2x80x94C1-C4alkyl- or N,N- di- C1-C4alkylamino which are unsubstituted or substituted in the alkyl moiety by hydroxyl, C1-C4alkoxy, carboxyl, cyano, halogen, sulfo, sulfato, phenyl or sulfophenyl, for example methylamino, ethylamino, N,N-dimethylamino, N,N-diethylamino, xcex2-cyanoethylamino, xcex2-hydroxyethylamino, N,N-di-xcex2-hydroxyethylamino, xcex2-sulfoethylamino, xcex3-sulfo-n-propylamino, xcex2-sulfatoethylamino, N-(3-sulfobenzyl)amino or N-ethyl-N-(3-sulfobenzyl)amino, N-(xcex2-sulfoethyl)-N-benzylamino; cyclohexylamino; N-phenylamino or Nxe2x80x94C1-C4alkyl-N-phenylamino which are unsubstituted or substituted in the phenyl moiety by nitro, C1-C4alkyl, C1-C4alkoxy, carboxyl, halogen or sulfo; C1-C4alkoxycarbonyl, for example methoxy- or ethoxycarbonyl; trifluoromethyl; nitro; cyano; halogen, which is to be understood generally as meaning, for example, fluorine, bromine or, in particular chlorine; ureido, hydroxyl, carboxyl, sulfo; sulfomethyl; carbamoyl; Nxe2x80x94C1-C4alkylcarbamoyl, for example N-methylcarbamoyl or N-ethylcarbamoyl; carbamido; sulfamoyl; Nxe2x80x94C1-C4alkylsulfamoyl, for example N-methylsulfamoyl or N-ethylsulfamoyl; N-phenylsulfamoyl or Nxe2x80x94C1-C4alkyl-N-phenylsulfamoyl; which are unsubstituted or substituted in the phenyl moiety by sulfo or carboxyl; and C1-C4alkylsulfonyl, for example methyl- or ethylsulfonyl;
which, with the exception of sulfo, are also further substituents in the benzene rings II, II or III.
Further substituents in the benzene rings I, II or III are preferably methyl, ethyl, methoxy, ethoxy, acetylamino, benzylamino, amino, chlorine, bromine, ureido, hydroxyl, carboxyl or sulfomethyl, and in particular methyl, ethyl, methoxy, ethoxy, chlorine, bromine, hydroxyl or carboxyl.
Fibre-reactive radicals are also substituents of the radicals D1 and D2.
Fibre-reactive radicals are to be understood as meaning those which are capable of reacting with the hydroxyl groups of cellulose, the amino, carboxyl, hydroxyl and thiol groups in wool and silk, or with the amino and possibly carboxyl groups of synthetic polyamides to form covalent chemical bonds. The fibre-reactive radicals are as a rule bonded to the dye radical directly or by a bridged member. Suitable fibre-reactive radicals are, for example, those which contain at least one substituent which can be split off on an aliphatic, aromatic or heterocyclic radical, or in which the radicals mentioned contain a radical which is suitable for reaction with the fibre material, for example a vinyl radical.
Preferred fibre-reactive radicals for D1 and D2 are the radicals of the formula (4a), (4b), (4c), (4d), (4e), (4f) or (4g)
xe2x80x94SO2xe2x80x94Yxe2x80x83xe2x80x83(4a),
xe2x80x94NHxe2x80x94COxe2x80x94(CH2)lxe2x80x94SO2xe2x80x94Yxe2x80x83xe2x80x83(4b),
xe2x80x94CONR8xe2x80x94(CH2)mxe2x80x94SO2xe2x80x94Yxe2x80x83xe2x80x83(4c),
xe2x80x94NHxe2x80x94COxe2x80x94CH(Hal)xe2x80x94CH2-Halxe2x80x83xe2x80x83(4d),
xe2x80x94NHxe2x80x94COxe2x80x94C(Hal)xe2x95x90CH2xe2x80x83xe2x80x83(4e),

in which
Hal is chlorine or bromine;
X2 is halogen, 3-carboxypyridin-1-yl or 3-carbamoylpyridin-1-yl;
T1 independently is as defined for X2 or is a substituent which is not fibre-reactive or a fibre-reactive radical of the formula (5a), (5b), (5c), (5d), (5e) or (5f) 
xe2x80x83in which
R8 and R10 independently of one another are each hydrogen, C1-C4alkyl which is unsubstituted or substituted by hydroxyl, sulfo, sulfato, carboxyl or cyano or a radical 
xe2x80x83R9 and R12 independently of one another are each hydrogen or C1-C4alkyl,
R11, is hydrogen, hydroxyl, sulfo, sulfato, carboxyl, cyano, halogen, C1-C4alkoxycarbonyl, C1-C4alkanoyloxy, carbamoyl or the group xe2x80x94SO2xe2x80x94Y,
alk and alk1 independently of one another are linear or branched C1-C6alkylene,
arylen is a phenylene or naphthylene radical which are unsubstituted or substituted by sulfo, carboxyl, C1-C4alkyl, C1-C4alkoxy or halogen,
Q is a radical xe2x80x94Oxe2x80x94 or xe2x80x94NR12xe2x80x94, in which R12 is as defined above,
W is a group xe2x80x94SO2xe2x80x94NR8xe2x80x94, xe2x80x94CONR8xe2x80x94 or xe2x80x94NR8COxe2x80x94, in which R8 is as defined above,
Y is vinyl or a radical xe2x80x94CH2xe2x80x94CH2xe2x80x94U and U is a group which can be split off under alkaline conditions,
Y1 is a group xe2x80x94CH(Hal)- CH2- Hal or xe2x80x94C(Hal)xe2x95x90CH2 and Hal is chlorine or bromine and
l and m independently of one another are an integer from 1 to 6 and n is the number 0 or 1; and
X3 is halogen or C1-C4alkylsulfonyl;
X4 is halogen or C1-C4alkyl and
T2 is hydrogen, cyano or halogen.
A group U which can be split off under alkaline conditions is, for example, xe2x80x94Cl, xe2x80x94Br, xe2x80x94F, xe2x80x94OSO3H, xe2x80x94SSO3H, xe2x80x94OCOxe2x80x94CH3, xe2x80x94OPO3H2, xe2x80x94OCOxe2x80x94C6H5, xe2x80x94OSO2xe2x80x94C1xe2x80x94C4alkyl or xe2x80x94C4alkyl)2. U is preferably a group of the formula xe2x80x94Cl, xe2x80x94OSO3H, xe2x80x94SSO3H, xe2x80x94OCOxe2x80x94CH3, xe2x80x94OCOxe2x80x94C6H5 or xe2x80x94OPO3H2, in particular xe2x80x94Cl or xe2x80x94OSO3H, and particularly preferably xe2x80x94OSO3H.
Examples of suitable radicals Y are accordingly vinyl, xcex2-bromo- or xcex2-chloroethyl, xcex2-acetoxyethyl, xcex2-benzoyloxyethyl, xcex2-phosphatoethyl, xcex2-sulfatoethyl and xcex2-thiosulfatoethyl. Y is preferably vinyl, xcex2-chloroethyl or xcex2-sulfatoethyl, and in particular vinyl or xcex2-sulfatoethyl.
R8 and R10 independently of one another are preferably hydrogen or C1-C4alkyl, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl and particularly preferably hydrogen, methyl or ethyl. R8 and R10 are particularly preferably hydrogen.
R9 and R12 independently of one another are each preferably hydrogen, methyl or ethyl, and particularly preferably hydrogen.
R11 is preferably hydrogen.
l and m independently of one another are preferably the number 2, 3 or 4, and particularly preferably the number 2 or 3.
Especially preferably, l is the number 3 and m is the number 2.
A non-reactive substituent T1 can be, for example, hydroxyl; C1-C4alkoxy; C1-C4alkylthio which is unsubstituted or substituted by hydroxyl, carboxyl or sulfo; amino; amino which is mono- or disubstituted by C1-C8alkyl, in which the alkyl is unsubstituted or further substituted, for example, by sulfo, sulfato, hydroxyl, carboxyl or phenyl, in particular by sulfo or hydroxyl, and may be interrupted by a radical xe2x80x94Oxe2x80x94; cyclohexylamino; morpholino; Nxe2x80x94C1-C4alkyl-N-phenylamino or phenylamino or naphthylamino, in which the phenyl or naphthyl are unsubstituted or substituted, for example by C1-C4-alkyl, C1-C4-alkoxy, carboxyl, sulfo or halogen.
Examples of suitable non-reactive substituents T1 are amino, methylamino, ethylamino, xcex2-hydroxyethylamino, N,N-di-xcex2-hydroxyethylamino, xcex2-sulfoethylamino, cyclohexylamino, morpholino, 2-, 3- or 4-chlorophenylamino, 2-, 3- or 4-methylphenylamino, 2-, 3- or 4-methoxyphenylamino, 2-, 3- or 4-sulfophenylamino, disulfophenylamino, 2-, 3- or 4-carboxyphenylamino, 1- or 2-naphthylamino, 1-sulfo-2-naphthylamino, 4,8-disulfo-2-naphthylamino, N-ethyl-N-phenylamino, N-methyl-N-phenylamino, methoxy, ethoxy, n- or iso-propoxy and hydroxyl.
A radical T1 which is not fibre-reactive is preferably C1-C4alkoxy, C1-C4-alkylthio which is unsubstituted or substituted by hydroxyl, carboxyl or sulfo, hydroxyl, amino, N-mono- or N,N-di-C1-C4alkylamino which are unsubstituted or substituted in the alkyl moiety by hydroxyl, sulfato or sulfo, morpholino, phenylamino or Nxe2x80x94C1-C4alkyl-N-phenylamino, which are unsubstituted or substituted in the phenyl ring by sulfo, carboxyl, acetylamino, chlorine, methyl or methoxy and in which the alkyl is unsubstituted or substituted by hydroxyl, sulfo or sulfato, or naphthylamino which is unsubstituted or substituted by 1 to 3 sulfo groups.
Particularly preferred radicals T1 which are not fibre-reactive are amino, N-methylamino, N-ethylamino, N-xcex2-hydroxyethylamino, N-methyl-N-xcex2-hydroxyethylamino, N-ethyl-N-xcex2-hydroxyethylamino, N,N-di-xcex2-hydroxyethylamino, morpholino, 2-, 3- or 4-carboxyphenylamino, 2-, 3- or 4-sulfophenylamino or Nxe2x80x94C1-C4-alkyl-N-phenylamino.
Halogen X2 is, for example, fluorine, chlorine or bromine, and in particular chlorine or fluorine.
X2 is preferably chlorine or fluorine.
Halogen T2, X3 and X4 are, for example, fluorine, chlorine or bromine, in particular chlorine or fluorine.
C1-C4alkylsulfonyl X3 is, for example, ethylsulfonyl or methylsulfonyl, and in particular methylsulfonyl.
C1-C4alkyl X4 is, for example, methyl, ethyl, n- or iso-propyl or n-, iso- or tert-butyl, and in particular methyl.
X3 and X4 are preferably independently of one another chlorine or fluorine.
T2 is preferably cyano or chlorine.
Hal is preferably bromine.
Alk and alk1 independently of one another are, for example, a methylene, ethylene, 1,3-propylene, 1,4-butylene, 1,5-pentylene or 1,6-hexylene radical or branched isomers thereof.
Alk and alk1 independently of one another are preferably each a C1-C4alkylene radical, and particularly preferably an ethylene or propylene radical.
Arylen is preferably a 1,3- or 1,4-phenylene radical which is unsubstituted or substituted, for example by sulfo, methyl, methoxy or carboxyl, and particularly preferably an unsubstituted 1,3- or 1,4-phenylene radical.
Q is preferably xe2x80x94NHxe2x80x94 or xe2x80x94Oxe2x80x94, and particularly preferably xe2x80x94Oxe2x80x94.
W is preferably a group of the formula xe2x80x94CONHxe2x80x94 or xe2x80x94NHCOxe2x80x94, in particular a group of the formula xe2x80x94CONHxe2x80x94.
n is preferably the number 0.
The reactive radicals of the formulae (5a) to (5f) are preferably those in which W is a group of the formula xe2x80x94CONHxe2x80x94, R10, R11 and R12 are each hydrogen, Q is the radical xe2x80x94Oxe2x80x94 or xe2x80x94NHxe2x80x94, alk and alk1 independently of one another are each ethylene or propylene, arylen is phenylene which is unsubstituted or substituted by methyl, methoxy, carboxyl or sulfo, Y is vinyl or xcex2-sulfatoethyl, Y1 is xe2x80x94CHBrxe2x80x94CH2Br or xe2x80x94CBrxe2x95x90CH2 and n is the number 0.
Fibre-reactive radicals for D1 and D2 are particularly preferably radicals of the formula (4a), (4b), (4c), (4d), (4e) or (4f), in which Y is vinyl, xcex2-chloroethyl or xcex2-sulfatoethyl, Hal is bromine, R8 and R9 are hydrogen, l and m are the number 2 or 3, X2 is halogen, T1 is C1-C4alkoxy, C1-C4alkylthio which is unsubstituted or substituted by hydroxyl, carboxyl or sulfo, hydroxyl, amino, N-mono- or N,N- di- C1-C4-alkylamino which are unsubstituted or substituted in the alkyl moiety by hydroxyl, sulfato or sulfo, morpholino, phenylamino or Nxe2x80x94C1-C4alkyl-N-phenylamino which are unsubstituted or substituted in the phenyl ring by sulfo, carboxyl, chlorine, acetylamino, methyl or methoxy and in which the alkyl is unsubstituted or substituted by hydroxyl, sulfo or sulfato, naphthylamino which is unsubstituted or substituted by 1 to 3 sulfo groups, or a fibre-reactive radical of the formula (5axe2x80x2), (5bxe2x80x2), (5cxe2x80x2), (5dxe2x80x2) or (5fxe2x80x2)
xe2x80x94NHxe2x80x94(CH2)2-3xe2x80x94SO2Yxe2x80x83xe2x80x83(5axe2x80x2),
xe2x80x94NHxe2x80x94(CH2)2-3xe2x80x94Oxe2x80x94(CH2)2-3xe2x80x94SO2Yxe2x80x83xe2x80x83(5bxe2x80x2),

in particular a fibre-reactive radical of the formula (5cxe2x80x2) or (5dxe2x80x2), in which
Y is vinyl, xcex2-chloroethyl or xcex2-sulfatoethyl and
Y1 is a group xe2x80x94CH(Br)xe2x80x94CH2xe2x80x94Br or xe2x80x94C(Br)xe2x95x90CH2.
In the case of the radicals of the formula (5axe2x80x2) and (5bxe2x80x2), Y is preferably xcex2-chloroethyl. In the case of the radicals of the formulae (5cxe2x80x2) and (5dxe2x80x2), Y is preferably vinyl or xcex2-sulfatoethyl.
D1 and D2 preferably contain at least one fibre-reactive radical.
D1 and D2 are preferably a phenyl or naphthyl radical which are unsubstituted or further substituted by substituents customary in dyes, for example C1-C4alkyl, C1-C4alkoxy, halogen, sulfo, nitro, carboxyl or a fibre-reactive radical of the formula (4a), (4b), (4c), (4d), (4e), (4f) or (4g), where the fibre-reactive radicals mentioned are as defined and preferred above.
A radical D1 or D2 of a substituted or unsubstituted diazo component of the benzene or naphthaline series also includes monoazo radicals, for example those of the formula (6) or (7)
xe2x80x94D*xe2x80x94Nxe2x95x90Nxe2x80x94K*xe2x80x83xe2x80x83(6)
or
D*xe2x80x94Nxe2x95x90Nxe2x80x94K**xe2x80x94xe2x80x83xe2x80x83(7),
preferably of the formula (7), in which D* is the radical of a diazo component of the benzene or naphthaline series, K* is the radical of a coupling component of the benzene, naphthaline, pyrazolone, 6-hydroxypyrid-2-one or acetoacetic acid arylamide series and K** is the radical of the coupling component of the benzene or naphthaline series, where D*, K* and K** can carry substituents customary in dyes.
Substituents for D*, K* and K** which are not fibre-reactive are preferably C1-C4alkyl or C1-C4alkoxy which are unsubstituted or further substituted by hydroxyl, C1-C4alkoxy, sulfo or sulfato, halogen, carboxyl, sulfo, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, amino, ureido, hydroxyl, sulfomethyl, C2-C4alkanoylamino, C1-C4alkylsulfonylamino, benzoylamino which is unsubstituted or substituted in the phenyl ring by C1-C4alkyl, C1-C4alkoxy, halogen or sulfo or phenyl which is unsubstituted or substituted by C1-C4alkyl, C1-C4alkoxy, halogen, carboxyl or sulfo.
Fibre-reactive substituents for D*, K* and K** a re preferably the radicals of the formula (4a), (4c), (4d), (4e) or (4f), in particular (4a), where the radicals mentioned are as defined and preferred above.
The monoazo radicals of the formula (6) or (7) preferably contain at least one sulfo group.
Preferred monoazo radicals D1 and D2 of the formula (7) are the radicals of the formula (7a), (7b), (7c), (7d), (7e), (7f), (7g), (7h), (7i) or (7j) 
in which (R13)0-2 is 0 to 2 identical or different substituents from the group consisting of C1-C4alkyl, C1-C4alkoxy, halogen, carboxyl and sulfo and Z1, is a fibre-reactive radical of the formula (4a), (4c), (4d), (4e) or (4f), where the fibre-reactive radicals mentioned are as defined and preferred above, 
in which (R13)0-2 is as defined above, (R14)0-3 is 0 to 3 identical or different substituents from the group consisting of halogen, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C1-C4alkyl, C1-C4alkoxy which is unsubstituted or substituted by hydroxyl, sulfato or C1-C4alkoxy, amino, C2-C4alkanoylamino, ureido, hydroxyl, carboxyl, sulfomethyl, C1-C4alkylsulfonylamino, sulfo and a fibre-reactive radical of the formula (4fxe2x80x2) 
in which
Xxe2x80x22 is fluorine or chlorine and
Txe2x80x21 is amino, N-mono- or N,N- di- C1-C4alkylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, sulfato or sulfo, morpholino, phenylamino or Nxe2x80x94C1-C4alkyl-N-phenylamino which are unsubstituted or substituted in the phenyl ring by sulfo, carboxyl, acetylamino, chlorine, methyl or methoxy and in which the alkyl is unsubstituted or substituted by hydroxyl, sulfo or sulfato or naphthylamino which is unsubstituted or substituted by 1 to 3 sulfo groups and
Z1 is as defined above.
The numbers on the naphthyl rings of the radicals of the formulae (7a), (7b), (7e) and (7f) identify the possible bonding positions.
The radicals D1 and D2 independently of one another are preferably each a radical of the formula (8) or (9) 
in particular of the formula (9), in which
(R13)0-2 and (R15)0-2 independently of one another are 0 to 2 identical or different substituents chosen from the group consisting of halogen, C1-C4alkyl, C1-C4alkoxy, carboxyl and sulfo;
K is the radical of a coupling component of the formula (10a) or (10b) 
in which
R14 is hydrogen, sulfo or C1-C4alkoxy which is unsubstituted or substituted in the alkyl moiety by hydroxyl or sulfato and
Rxe2x80x214 is hydrogen, C1-C4alkyl, C1-C4alkoxy, C2-C4alkanoylamino, ureido or a radical of the formula (4fxe2x80x2), in which Xxe2x80x22 and Txe2x80x21 are as defined above; and
Z and Z1 independently of one another are a radical of the formula (4a), (4b), (4c), (4d), (4e) or (4f), in which
R8 and R9 are hydrogen,
Hal is bromine,
Y is vinyl, xcex2-chloroethyl or xcex2-sulfatoethyl,
l and m independently of one another are the number 2 or 3,
X2 is chlorine or fluorine and
T1 is C1-C4alkoxy, C1-C4alkylthio which is unsubstituted or substituted by hydroxyl, carboxyl or sulfo, hydroxyl, amino, N-mono- or N,N- di- C1-C4alkylamino, which are unsubstituted or substituted in the alkyl moiety by hydroxyl, sulfato or sulfo, morpholino, phenylamino or Nxe2x80x94C1-C4alkyl-N-phenylamino which are unsubstituted or substituted in the phenyl ring by sulfo, carboxyl, acetylamino, chlorine, methyl or methoxy and in which the alkyl is unsubstituted or substituted by hydroxyl, sulfo or sulfato, naphthylamino which is unsubstituted or substituted by 1 to 3 sulfo groups, or a fibre-reactive radical of the formula (5cxe2x80x2) or (5dxe2x80x2) 
in which
Y is as defined above, and in particular is vinyl or xcex2-sulfatoethyl.
C1-C4alkyl R13, Rxe2x80x214 and R15 independently of one another are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl or isobutyl, preferably methyl or ethyl, and in particular methyl.
C1-C4alkoxy R13, R14, Rxe2x80x214 and R15 independently of one another are, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy, preferably methoxy or ethoxy, and in particular methoxy. R14 is unsubstituted or may be substituted in the alkyl moiety by hydroxyl or sulfato.
Halogen R13 and R15, independently of one another are, for example, fluorine, chlorine or bromine, preferably chlorine or bromine, and in particular chlorine.
C2-C4alkanoylamino Rxe2x80x214 is, for example, acetylamino or propionylamino, in particular acetylamino.
In the radical of the coupling component of the formula (10b), the sulfo group in ring ii is preferably bonded in the 3 or 4-position. If the ring ii contains a sulfo group, the radical of the formula (10b) is preferably bonded to ring ii in the 1, 2 or 3-position. If no sulfo is present in the ring ii, the radical of the formula (10b) is preferably bonded in the 1-, 2 or 3-position on ring ii.
The radicals D1 and D2 independently of one another are particularly preferably each a radical of the formula (9a), (9b), (9c), (9d), (9e) or (9f) 
in which (R15)0-2 and (R16)0-2 independently of one another are 0 to 2 identical or different substituents chosen from the group consisting of halogen, C1-C4alkyl, C1-C4alkoxy and sulfo, in particular methyl, methoxy and sulfo,
Y is vinyl, xcex2-chloroethyl or xcex2-sulfatoethyl,
Y1 is a group xe2x80x94CH(Br)xe2x80x94CH2xe2x80x94Br or xe2x80x94C(Br)xe2x95x90CH2,
l is the number 2 or 3, in particular 3, and
m is the number 2 or 3, in particular 2.
The numbers in the radicals of the formulae (9a), (9c), (9d), (9e) and (9f) identify the possible bonding positions of the fibre-reactive radical.
In the case of the radicals of the formulae (9a), (9b), (9d) and (9f), Y is preferably vinyl or xcex2-sulfatoethyl.
In the case of the radical of the formula (9c), Y is preferably xcex2-chloroethyl.
D1 and D2 independently of one another are preferably in each case a radical of the formula (9a) or (9b), and in particular (9a).
R2 is preferably hydrogen or C1-C4alkyl, particularly preferably hydrogen, methyl or ethyl, and especially preferably hydrogen.
R3 is preferably cyano or carbamoyl, and in particular cyano.
C1-C4alkyl R4 and R7 independently of one another are, for example, methyl, ethyl, n- or iso-propyl or n-, sec-, tert- or iso-butyl, preferably methyl or ethyl, and in particular methyl.
R4 is preferably methyl, ethyl or amino, and in particular methyl.
N-Mono- or N,Nxe2x80x94dixe2x80x94C1-C4alkylamino R5 is unsubstituted or substituted in the alkyl moiety, for example by C1-C4alkyl, C1-C4alkoxy, C2-C4alkanoylamino, hydroxyl, sulfo, sulfato or carboxyl, preferably hydroxyl, sulfo or sulfato, and in particular hydroxyl. Examples are the following radicals: N-methylamino, N,N-dimethylamino, N-ethylamino, N-xcex2-hydroxyethylamino, N,N-di-xcex2-hydroxyethylamino, N-xcex2-sulfatoethylamino, N-xcex2-sulfoethylamino or N-xcex2-carboxyethylamino.
R5 is preferably amino or N-mono-C1-C4alkylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, sulfo or sulfato, and in particular amino or N-xcex2-hydroxyethylamino.
R6 is preferably carbamoyl or sulfomethyl, in particular carbamoyl.
R7 is preferably methyl or ethyl, and in particular methyl.
The formazan radical in the dye of the formula (1) is preferably a radical of the formula (11) or (12) 
preferably a radical of the formula (12).
The formazan radicals in the dyes of the formula (1) according to the invention are particularly preferably the radicals of the formula (12a) or (12b) 
in particular (12a).
The dyes of the formula (1) according to the invention preferably have the formula (1a) 
in which
X1 is fluorine or chlorine,
R1 is hydrogen or R1 is as defined for A and
A is a radical of the formula (2axe2x80x2), (2bxe2x80x2) or (3a) 
xe2x80x83in which
B1 and B2 are straight-chain or branched C2-C6alkylene,
D1 and D2 independently of one another are each a radical of the formula (9a), (9b), (9c), (9d), (9e) or (9f), where the radicals mentioned are as defined and preferred above,
R5 is amino or N-xcex2-hydroxyethylamino and
R6 is carbamoyl or sulfomethyl, in particular carbamoyl.
The dyes of the formula (1), according to the invention particularly preferably have the formula (1axe2x80x2) 
in which
X1, R1, and A are as defined and preferred above under formula (1a).
The present invention furthermore relates to a process for the preparation of the dyes according to the invention, which comprises reacting in each case about 1 molar equivalent of a compound of the formula (13) 
a compound of the formula (14) 
and an amine of the formula (15) 
with one another in any sequence, where A, Me, R1, u and q are as defined and preferred above and X is halogen, in particular fluorine or chlorine.
The individual process steps defined above can be carried out in various sequences, and where appropriate in some cases also simultaneously, so that various process variants are possible. In general, the reaction is carried out stepwise in succession, the sequence of the simple reactions between the individual reaction components advantageously depending on the particular conditions.
One process variant comprises subjecting a compound of the formula (13) to a condensation reaction with cyanuric chloride or cyanuric fluoride and reacting the resulting product with a compound of the formula (15).
The condensation reactions between the compounds of the formulae (13), (14) and (15) in general are carried out analogously to known processes, as a rule in aqueous solution at temperatures of, for example, 0 to 30xc2x0 C. and a pH of, for example, 3 to 7. Instead of the compound of the formula (15), it is also possible to employ the corresponding intermediate of the formula (17a), (17b) or (18) 
in the process and to produce the radical A only in the subsequent course of the process, by diazotization of an amine of the formula (16a) or (16b)
D1xe2x80x94NH2xe2x80x83xe2x80x83(16a)
or
D2xe2x80x94NH2xe2x80x83xe2x80x83(16b)
and subsequent coupling reactions. The radicals B1, B2, D1, D2, R2, R3, R4, R5, R6 and R7 are as defined above.
The compound of the formula (15) in which A is a radical of the formula (2a), (2b) or (3) is obtained by diazotizing an amine of the formula (16a) and coupling the diazotization product to a compound of the formula (17a) or (17b), or by diazotizing an amine of the formula (16b) and coupling the diazotization product to a compound of the formula (18).
The diazotization of the compound of the formula (16a) or (16b) and its coupling to the compound of the formula (17a), (17b) or (18), or to the condensation product obtained according to the procedure described above from the compound of the formula (17a), (17b) or (18) are carried out in the customary manner, for example by diazotizing the compound of the formula (16a) or (16b) in mineral acid solution, for example hydrochloric acid solution, with a nitrite, for example sodium nitrite, at a low temperature, for example at 0 to 5xc2x0 C., and then coupling the diazotization product with the corresponding coupling component at a neutral to slightly acid pH, for example at pH 3 to 7, and low temperatures, for example 0 to 30xc2x0 C.
The compounds of the formulae (13), (16a), (16b), (17a), (17b) and (18) are known or can be prepared analogously to known compounds.
The compounds of the formulae (17a) and (17b) as a rule are obtained as a mixture in the preparation.
The triazinyl compounds obtainable by the process described above still contain a halogen atom which can be converted into a group X1 by reaction with a compound of the formulae X1-H at elevated temperature, preferably 20 to 70xc2x0 C., and a neutral to slightly alkaline pH, which is, for example, 7 to 9, depending on the compound of the formula X1-H employed, where X1 is as defined above, except for halogen. An excess of the compound of the formula X1-H is advantageously employed.
If appropriate, the end product can also be subjected to a conversion reaction. Such a conversion reaction is, for example, the conversion of a vinylatable reactive group contained in D1 or D2 into its vinyl form by treatment with dilute sodium hydroxide solution, for example conversion of the xcex2-sulfatoethylsulfonyl- or xcex2-chloroethylsulfonyl group into the vinylsulfonyl radical. Such reactions are known per se.
The compounds of the formula (1) according to the invention are suitable as dyes for dyeing and printing widely varying materials, such as fibre materials containing hydroxyl groups or containing nitrogen. Examples of fibre materials containing nitrogen are silk, leather, wool, polyamide fibres and polyurethanes. The dyes according to the invention are particularly suitable for dyeing and printing all types of cellulosic fibre materials. Such cellulosic fibre materials are, for example, the natural cellulose fibres, such as cotton, linen and hemp, and pulp and regenerated cellulose, preferably cotton. The dyes according to the invention are also suitable for dyeing or printing cellulosic blend fabrics, for example mixtures of cotton and polyamide fibres, or in particular cotton/polyester blends.
The dyes according to the invention can be applied to the fibre material and fixed on the fibre in various ways, in particular in the form of aqueous dye solutions and printing pastes. They are suitable both for the exhaust method and for dyeing by the padder dyeing method, in which the goods are impregnated with aqueous dye solutions, which may contain salts, and the dyes are fixed, after an alkali treatment or in the presence of alkali, if appropriate with the action of heat or by storage at room temperature for several hours. After the fixing, the dyeings or prints are rinsed thoroughly with cold and hot water, if appropriate with the addition of an agent which has a dispersing action and promotes diffusion of the non-fixed portions.
The dyes according to the invention are distinguished by a high reactivity, good fixing capacity and very good build-up capacity. They can therefore be employed by the exhaust dyeing method at low dyeing temperatures and require only short steaming times in the pad-steam process. The degrees of fixing are high and the non-fixed portions can easily be washed out, the difference between the degree of exhaustion and degree of fixing being remarkably small, i.e. the soaping loss being very low. The dyes according to the invention are also particularly suitable for printing, in particular on cotton, and also for printing fibres containing nitrogen, for example wool or silk or blend fabrics which comprise wool or silk.
The dyeings and prints produced with the dyes according to the invention have a high colour strength and a high fibre-dye bond stability both in the acid and in the alkaline range, and furthermore a good fastness to light and very good wetfastness properties, such as fastness to washing, water, seawater, cross-dyeing and perspiration, and a good fastness to pleating, fastness to ironing and fastness to rubbing.